A solid-state fluorescent probe for α,β-diamine based on tetraphenylethylene skeleton construction

Abstract

α,β-Diamines, as raw materials or intermediates, have extensive applications in various chemical industries, but volatile amine vapors are serious threats to the environment and human health. So far, numerous fluorescent sensors have been developed to detect amines, but a majority of them are based on aggregation-caused quenching or lack portability. As a fluorescent dye with aggregation-induced emission property, the switching mechanism of tetraphenylethylene (TPE) and its application in chemical sensors have attracted considerable attention. In this research, we report a fluorescent sensor, namely DPEC, based on TPE, which showed response to α,β-diamines with high selectivity and sensitivity via the quinone-containing redox mechanism. When the sensor was exposed to amines, they underwent a Michael addition and redox reaction between the quinone units of the sensing material and the target amines to construct the TPE fluorophore, resulting in “turn-on” response and rapid color changes. As is known, this is the first fluorescent sensor based on the TPE skeleton construction. The research explored the TPE construction mechanism and will contribute to the development of novel TPE sensors.